1-Methylimidazole → 1-methyl-3-(1-methyl-2-phenyl-2-oxoethyl)-1H-imidazolium bromide

HRID 64656

Reaction equation

HRID 64656 reaction equation
[C:1]1([C:7](=[O:11])[CH:8]([Br:10])[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:12][N:13]1[CH:17]=[CH:16][N:15]=[CH:14]1>C(OCC)C>[Br-:10].[CH3:12][NH+:13]1[CH:17]=[CH:16][N:15]([CH:8]([CH3:9])[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:11])[CH2:14]1

Participants

4

Reactant 2

HCID 13901-MethylimidazoleHCID 164522-Bromopropiophenone

Product 1

HCID 703877441-methyl-3-(1-methyl-2-phenyl-2-oxoethyl)-1H-imidazolium bromideYield 55%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 8 ml (0.047 mol) of 90% pure 1-phenyl-1-oxo-2-bromopropane and 4.25 g (0.052 mol) of 1-methylimidazole in 100 ml of diethyl ether was stirred at room temperature for approximately 24 hours. The precipitated solid was collected by filtration, washed with diethyl ether and dissolved in methanol. This solution was diluted with diethyl ether and the resulting white solid was collected by filtration. This solid was recrystallized from methanol/diethyl ether to afford 7.65 g of 1-methyl-3-(1-methyl-2-phenyl-2-oxoethyl)-1H-imidazolium bromide as white crystals. (55% yield) mp=167°-170° C.

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. washwashed with diethyl ether
  3. dissolutiondissolved in methanol
  4. additionThis solution was diluted with diethyl ether
  5. filtrationthe resulting white solid was collected by filtration
  6. customThis solid was recrystallized from methanol/diethyl ether

Sources & evidence

ORD record
ord-adb1937ba43f4ec58485f7a79e1b4121
Source dataset
uspto-grants-1986_09
Patent number
US04609670

Linked notes

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